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The film is about a group of men experiencing a collective midlife crisis. Mitch Robbins (Crystal) is an advertising manager at a radio station who's increasingly disillusioned with the lack of meaning he sees in his job and his life. Phil Berquist (Stern) is stuck managing his father-in-law's grocery store, while trapped in a sexless marriage with an overbearing wife. And Ed Furillo (Kirby) is a successful businessman and playboy, struggling with the idea of monogamous marriage and the pressure to have kids.

At Mitch's 39th birthday party, Phil and Ed present their joint birthday present: a two-week Southwestern cattle drive for all three men. At the insistence of his wife Barbara (Patricia Wettig), Mitch accepts the gift, traveling with his friends to New Mexico, where they meet the other participants of the cattle drive and learn the ropes of moving the herd, guided by the grizzled, tough-as-nails boss of the whole operation, Curly (Palance).

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Jack Palance's performance as Curly won him the 1991 Academy Award for Best Supporting Actor and AFI ranked the film as #86 on its "100 Laugh" list. Followed in 1994 by City Slickers II: The Legend of Curly's Gold, which was not as well-received as the original.

Awful Wedded Life: All scenes and dialogue make it obvious that this is the case between Phil and Arlene.

Backup Twin: City Slickers II has this in the form of Duke, Curly's equally-scary twin brother. The reason given for his absence, and not even being mentioned, in the first movie is that he and Curly weren't on speaking terms, he was out on the sea, and Curly didn't exactly talk about his personal life to a guy he met yesterday all that much anyway.

The Chew Toy: Phil is never safe from the world's abuse. Examples include being chased by bulls to the point that he is forced to jump onto a flagpole, accidentally sitting on a cactus and mistaking it for a snake bite, or being involved in a sexless marriage.

Hollywood Mid-Life Crisis: The film about three friends who are each going through their own respective mid-life crisis. Mitch is bored with his job and frightened by how quickly the years seem to be flying by. Phil's Sexless Marriage prompts him to have an affair with a younger coworker, resulting in him losing his job and his wife leaving him. Ed is a successful businessman and womanizer who is frightened by the prospect of settling down and starting a family. The three friends go on a cattle drive vacation, during which they all begin to figure out their lives.

I Am Not My Father: Mitch suggests that Ed's drive to succeed comes from wanting to be better than the father who abandoned him and his mother and sister.

Conversely, his fears of commitment and fatherhood appear to be for the same reason—even after finally marrying, he's reluctant to have children out of fear of turning out like his father.

No Party Like a Donner Party: Discussed in II when the group is trying to deal with spending the night out in a freezing thunderstorm with no tent. The reaction to this suggestion by Mitch and Glen is about what you would expect, and eventually they come up with a better plan.

Phil: In case we don't make it, and I die first...eat me. Mitch: Eat you??? I don't even like to talk to you on the phone!

Polar Opposite Twins: Curly was the more honorable of the two, and also preferred the life of a cowboy. Duke was a conniving sort who loved the sea and joined the Navy. But they appear to have had a mutual respect and have equally threatening presences.

Reckless Gun Usage: Phil wrestles for one of the trail hands' guns and uses it to scare them into sobering up. Even after the situation has been defused (Phil yells "BANG!" instead of shooting), he keeps his finger tight on the trigger and is clearly agitated.

Speed Sex: Mitch does this with his wife in the sequel when he notices a piece of paper tucked away in Curly's cowboy hat. While his wife goes into the bathroom after the sex, Mitch pulls it out and notices that it is a secret treasure map.

Taking the Bullet: Parodied in City Slickers II when Glen takes a bullet for Mitch, shares some tearful last words with his brother, and black out...then immediately revives upon discovering the bullet was a blank.

Title Drop: Clay Stone tells the cattle drive group that "You came here city slickers; you're gonna go home cowboys."

Toros y Flamenco: The opening depicts Pamplona's annual Running of the Bulls. Although Phil and Ed flee from the bulls (Phil by jumping on a Spanish flagpole and Ed by getting into the spectators), Mitch gets gored from behind.

Treasure Map: Subverted in City Slickers IIsince it was a fake map leading to fake treasure as part of an "adventure tour." Then Double Subverted, when it turns out there was gold hidden elsewhere in the desert..

Unsettling Gender Reveal: Interspecies example in the second movie, when Glen decides to help out around the house by milking the cow Mitch acquired in the first movie:

Glen: There is something wrong with your cow. I reach under there and I'm pulling, tugging, tugging, pulling, nothing, not a drop. Mitch: The cow's name is Norman. You were pulling on his dick. Glen:I'm gonna go wash up.

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